Vice President - Tax

Company: Kingsway America Inc. (Holding Company)
Location: Itasca, IL
Department: Tax
Reports to: Chief Financial Officer
FLSA: Exempt


Kingsway Financial Services (“Kingsway”) is a publicly traded holding company (NYSE:  KFS). Kingsway aspires to compound intrinsic value per share at high rates over the long-term through efficient operations and thoughtful capital allocation. Kingsway owns or controls subsidiaries primarily in the extended warranty, asset management, and real estate industries.

The Vice President Tax has the primary responsibility for overseeing Kingsway’s significant net operating loss position (approximately $844 million) and advising management on strategies for effectively utilizing the NOLs.  The Vice President Tax also is responsible for Kingsway’s financial statement tax accounting, any federal and state income tax examinations, advising on the tax aspects of acquisitions and dispositions, overseeing all tax return compliance (outsourced), and tax research and planning matters of Kingsway and its subsidiaries.

To be successful as a Vice President Tax, he/she must be financially savvy, detail-oriented and organized, with good business judgment and strong communication and leadership skills, as well as the ability to build trustworthy relationships with staff, business partners and employees at all levels. He/she should also have strong analytical and problem-solving skills, as well as have a genuine sense of curiosity.

Major Responsibilities:

  • Communicate and discuss all significant tax matters affecting the Company’s financial statements with the Chief Financial Officer and Corporate Controller, including changes to the Company’s deferred tax valuation allowance, the tax aspects of purchase accounting for entities acquired by the Company and unrecognized tax benefit matters
  • Provide tax advice and assistance, as needed, for strategic initiatives, capital investments, growth opportunities, mergers and acquisitions and other special projects
  • Manage and closely monitor the Company’s ownership change calculations under Internal Revenue Code Section 382, as well as provide scenario analysis
  • Coordinate the preparation and review of all quarterly and annual GAAP and insurance regulatory tax provisions of the Company
  • Coordinate the preparation and review of all tax disclosures included in the financial statements of the Company, including those contained in GAAP and insurance regulatory financial statements, SEC filings, press releases and other public documents
  • Coordinate the preparation and review of the Company’s United States, foreign, state and local tax returns, including extension filings and estimated tax payments (outsourced)
  • Manage and monitor the Company’s risk associated with all tax positions taken in the Company’s tax returns
  • Establish and maintain effective working relationships with the financial/accounting managers of the Company’s business units
  • Comply with the internal control standards of Kingsway as it pertains to tax
  • Manage all income tax examinations of the Company by external governmental entities
  • Manage the Company’s tax relationship with the Company’s external auditors and all external tax and legal advisors
  • Coordinate the preparation and review of all tax calculations with regard to the Company’s intercompany federal income tax allocation agreement
  • Manage all tax research and planning for Kingsway
  • Special projects and other duties as assigned


  • Bachelor’s Degree in Accounting with Master’s Degree in Taxation preferred
  • 15+ years relevant work experience; CPA preferred
  • Public accounting background preferred but not required
  • Experience in Internal Revenue Code Section 382 modeling and planning is required
  • Experience in the tax aspects of mergers and acquisitions as well as the tax aspects of GAAP purchase accounting for acquired entities
  • Experience in GAAP deferred tax valuation allowance matters
  • Ability to effectively manage and mentor staff
  • Strong organizational awareness, interpersonal skills, and leadership skills
  • Ability to work well under pressure and independently, in order to meet strict deadlines
  • Ability to manage multiple tasks and changing priorities in a complex business environment
  • Excellent oral and written communication, organization, analytical and problem-solving skills
  • Interacts effectively with all levels of the organization and external parties
  • Develops effective working relationships across organizational lines
  • Excellent working knowledge of income tax preparation software and MS Office 365 software programs, including MS Word, Excel and Power Point
To apply, please send resume and cover letter to Yvonne Santana